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Despite his physical shortcomings, Hiccup does his best to succeed as a Viking. He is intelligent and is constantly creating inventions for various uses throughout the film, including a bola sling, a prosthetic tail, a saddle, and a riding vest. At first, however, Hiccup is obsessed with proving himself to the rest of his tribe by killing a dragon; he often doesn't think things through and is more determined to gain the recognition of his peers than he is heedful of others' orders, often causing problems for the rest of the tribe, and himself. Despite this, Hiccup shows great aptitude at being a leader and a strategist: he leads his Dragon Training classmates into battle, using his friends' strengths wisely in the battle against the Red Death. Hiccup also has very good observational skills which come in handy during his time with Toothless and during Dragon Training. For example, he's able to hypothesize that dragons have a natural disdain for eel when his own dragon companion refuses to eat one himself, and uses this to successfully drive back a Hideous Zippleback later.

Among the other teenage Vikings, Hiccup first comes off as awkward, mainly because he's a poor fighter, and rather scrawny for a Viking. As he becomes more adept at fighting dragons, however, they start paying more attention to him, some even starting to try to talk to him. Despite this, Hiccup remains shy and secretive, preferring to be alone with Toothless, likely because he's unused to all the positive attention. He also tends to be sarcastic with a dry sense of humor that can sometimes put him at odds with the other Vikings in his tribe. It also seems that Hiccup likes to hide his fear with said sarcasm and dry humor. Due to his shyness, he had a habit of stuttering and stammering when talking to some of the other Vikings, especially Astrid or when his father was angry at him. Despite his many virtues and his clear capabilities as a leader, Hiccup is not without his flaws. He is rather prone to letting his insecurities cloud his judgment and effect his actions; in the film, his desperation for the acceptance of his tribe, and his father in particular, cause him to regularly attempt to kill dragons along with the villagers, only to end up doing more harm then good due to his clumsiness. In the television show, his mistaken belief that Stoick still does not accept him causes him to lead the other Vikings on a potentially dangerous treasure hunt to prove himself. His innate friendliness and tendency to give others the benefit of the doubt cause him to be a little too trusting of strangers, leaving him vulnerable to manipulation and deceit by more dishonest characters, such as Heather and Mildew, on more then one occasion. In the episode Thawfest, Hiccup shows a more unlikable, competitive side of his personality as he begins to score victories over Snotlout. Since Hiccup is unaccustomed to winning anything, he handles it poorly, letting the glory go to his head to the point where he becomes just as arrogant and unpleasant as Snotlout. Hiccup is also prone to overconfidence in his ability as a diplomat due to being mostly successful so far, which becomes a major catalyst of the second film's story line; his total belief that he would be able to reason with Drago causes him to run away from Berk to confront the warlord, causing Stoick and Valka, who both understood and witnessed firsthand the true extent of Drago's psychopathy and knew he could not be reasoned with, to chase after him. This indirectly but ultimately leads to Stoick's death at the hands of Drago when he hypnotizes Toothless into attacking Hiccup to demonstrate the superiority of his philosophy over Hiccup's. In spite of all his flaws, Hiccup is never above admitting when he is or has been wrong, and will do his best to make amends with others.

One extremely notable character trait Hiccup possesses is a deep sense of compassion. Because of this he spares Toothless, and in doing so he changes the world of Vikings and dragons forever. He was extremely uncomfortable with the thought of having to kill a dragon in the arena later in the film. Hiccup carries this quality into the television series. He shows great sympathy to Snotlout at the end of the Thawfest Games, giving up his own glory and fame for the sake of his friend. He will almost never allow Toothless to use his full power against foes. In What Flies Beneath, he begs Toothless to spare a Whispering Death that had nearly killed both of them just moments earlier. The peak of Hiccup's sympathy is displayed in his releasing Mildew, the very man who had betrayed him, from an Outcast cell. Upon seeing the Outcasts take Mildew's one beloved possession, his sheep, Hiccup clearly displays pity for the old man. Unfortunately Hiccup is occasionally naïve in his sympathy, as Mildew betrayed him yet again right afterwards. Still, his kindheartedness has resulted in many a victory and accomplished the training of the deadliest dragons in the world. The one character Hiccup seems to be willing to attack and even kill is Alvin. Originally, Hiccup was more interested in avoiding him, but as Alvin's plots hit closer and closer to everything Hiccup cares about, Hiccup seems to harden in a difficult resolution. He has been seen ordering Toothless to kill Alvin when Alvin was threatening to toss Astrid off of a cliff. In the finale, Hiccup and Toothless even charged Alvin in an attempt to kill him after he had captured, threatened, and deeply insulted both of them. Although they failed in this attempt, Alvin is still one of the few people Hiccup is willing to let Toothless kill. Overall, Hiccup is an intelligent, nice and likable person who is naturally bighearted and innocent. It's shown in the sequel that he and Toothless have become "adrenaline junkies", performing tricks like free-falling. He has also gone from being a shy boy, to a confident young man, and "the greatest Dragon Master this world has ever seen" (as Astrid describes him to Drago Bludvist ) and he is shown to care for his loved ones, especially Stoick, Valka, Toothless and Astrid.

In the film, Hiccup's appearance is slightly different from the books. He's rather scrawny for his age, compared to the other Vikings, especially since he has little physical strength as he's barely able to lift a large axe, and isn't very tall, just being barely aroundAstrid's height. He has auburn hair parting to his right with minor freckles on his cheeks. If you look closely, you'll notice he has a small, white scar just below his bottom lip (which he got from when he was a baby, the night Cloudjumper took his mother away). He's usually seen wearing a long-sleeve, light-green tunic and a dark brown fur vest that matches with his boots. When he rides Toothless, he takes off his vest and wears a flying vest to help him stay on Toothless. After Dragon Training, he starts to wear a Viking helmet given to him by his father as shown in Gift of the Night Fury, made from half of his mother's breast plate (Stoick owning and wearing the other half). Following the battle with the Red Death, Hiccup's left leg up to his shin is replaced with a prosthetic made by Gobber with a metal foot and spring, which is accessible for flying with Toothless.

If observed closely, it can be noticed that his hair has slightly grown betweenRiders of Berk andDefenders of Berkand he is still wearing his light brown vest and boot. In Dawn of the Dragon Racers, Hiccup wear a similar type of his armor which is dark brown along a long-sleeve dark green tunic with brown arm brackets and later he wears an red orange tunic, in Race to the Edge.

In How to Train Your Dragon 2, Hiccup has noticeably grown considerably. He's now the tallest of the teens at 6'1" and his hair is somewhat scraggy and unkempt with two small braids behind his right ear. He seems to have gained a leaner, stronger build as compared to the first movie and is no longer considered a runt. His prosthetic is also different, as it's more mechanical and designed than before, making it like "a Swiss army knife for prosthesis", as Hiccup seems to have improved its ability (as he stated he would in the first movie). His outfit now is partly leather around his upper body with what appears to be a type of armor along with arm brackets that seem to all be designed by himself, making him look more like Toothless. When flying with Toothless now, he's also seen wearing a spiked masked when he glides in the air, as his outfit doubles as a squirrel jacket capable of gliding. His pants are dark brown and has straps around them with a leather boot for his right foot. He also carries a weapon, a fire blade called Inferno. And has a clip for his Lightsaber too.